data_2012120 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 996 _journal_page_last 998 _publ_section_title ; Conformational polymorphs of the N-methylamide of 2-cyano-5-phenylpent-2-en-4-ynoic acid ; loop_ _publ_author_name 'Borbulevych, Oleg Ya.' 'Golding, Igor R.' 'Shchegolikhin, Alexander N.' 'Klemenkova, Zinaida S.' 'Antipin, Mikhail Yu.' _chemical_formula_moiety 'C13 H10 N2 O' _chemical_formula_sum 'C13 H10 N2 O' _chemical_formula_weight 210.23 _chemical_melting_point 384 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.652(12) _cell_length_b 9.728(7) _cell_length_c 10.269(5) _cell_angle_alpha 90 _cell_angle_beta 97.29(4) _cell_angle_gamma 90 _cell_volume 2245(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.244 _diffrn_ambient_temperature 293(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .51989(9) .1326(2) .65637(18) .0714(6) Uani d . 1 . . O N1 .40660(13) .5274(3) .5243(3) .0824(8) Uani d . 1 . . N N2 .52030(9) .3542(2) .72239(19) .0545(6) Uani d . 1 . . N H2 .5022 .4320 .7122 .065 Uiso calc R 1 . . H C1 .50077(11) .2491(3) .6456(2) .0490(6) Uani d . 1 . . C C2 .45142(11) .2854(3) .5377(2) .0476(6) Uani d . 1 . . C C3 .43153(11) .1924(3) .4453(2) .0555(7) Uani d . 1 . . C H3 .4479 .1046 .4507 .067 Uiso calc R 1 . . H C4 .38672(12) .2227(3) .3404(2) .0536(7) Uani d . 1 . . C C5 .34816(12) .2549(3) .2550(2) .0519(7) Uani d . 1 . . C C6 .42675(12) .4201(3) .5295(2) .0558(7) Uani d . 1 . . C C7 .30001(11) .2962(3) .1603(2) .0462(6) Uani d . 1 . . C C8 .27396(13) .4228(3) .1721(3) .0664(8) Uani d . 1 . . C H8 .2894 .4825 .2387 .080 Uiso calc R 1 . . H C9 .22506(14) .4615(4) .0858(3) .0778(9) Uani d . 1 . . C H9 .2074 .5468 .0946 .093 Uiso calc R 1 . . H C10 .20243(13) .3740(4) -.0132(3) .0694(9) Uani d . 1 . . C H10 .1689 .3994 -.0701 .083 Uiso calc R 1 . . H C11 .22856(13) .2512(3) -.0285(3) .0632(8) Uani d . 1 . . C H11 .2138 .1939 -.0975 .076 Uiso calc R 1 . . H C12 .27716(12) .2101(3) .0581(2) .0546(7) Uani d . 1 . . C H12 .2946 .1248 .0479 .066 Uiso calc R 1 . . H C13 .57174(12) .3410(3) .8237(3) .0679(8) Uani d . 1 . . C H13A .5790 .2455 .8432 .102 Uiso calc R 1 . . H H13B .5637 .3880 .9018 .102 Uiso calc R 1 . . H H13C .6061 .3807 .7926 .102 Uiso calc R 1 . . H O1' 1.01898(9) .7563(2) .68323(15) .0689(6) Uani d . 1 . . O N1' .89839(14) .6122(4) .3035(3) .1193(14) Uani d . 1 . . N N2' 1.01957(9) .7867(2) .46670(17) .0479(5) Uani d . 1 . . N H2' 1.0037 .7650 .3889 .058 Uiso calc R 1 . . H C1' .99860(11) .7301(3) .5693(2) .0446(6) Uani d . 1 . . C C2' .94784(10) .6320(3) .5402(2) .0455(6) Uani d . 1 . . C C3' .92944(12) .5580(3) .6369(2) .0576(7) Uani d . 1 . . C H3' .9508 .5691 .7197 .069 Uiso calc R 1 . . H C4' .88133(13) .4649(3) .6277(3) .0581(7) Uani d . 1 . . C C5' .84124(13) .3868(3) .6332(3) .0554(7) Uani d . 1 . . C C6' .91935(13) .6196(3) .4093(3) .0668(8) Uani d . 1 . . C C7' .79511(11) .2901(3) .6496(2) .0478(6) Uani d . 1 . . C C8' .73735(12) .3048(3) .5861(3) .0588(7) Uani d . 1 . . C H8' .7283 .3764 .5269 .071 Uiso calc R 1 . . H C9' .69395(13) .2145(3) .6104(3) .0719(9) Uani d . 1 . . C H9' .6554 .2252 .5684 .086 Uiso calc R 1 . . H C10' .70703(14) .1083(3) .6964(3) .0733(9) Uani d . 1 . . C H10' .6772 .0480 .7139 .088 Uiso calc R 1 . . H C11' .76401(14) .0903(3) .7570(3) .0699(8) Uani d . 1 . . C H11' .7730 .0158 .8129 .084 Uiso calc R 1 . . H C12' .80749(12) .1811(3) .7356(3) .0570(7) Uani d . 1 . . C H12' .8458 .1699 .7790 .068 Uiso calc R 1 . . H C13' 1.06840(12) .8841(3) .4823(3) .0603(7) Uani d . 1 . . C H13D 1.0622 .9495 .5493 .091 Uiso calc R 1 . . H H13E 1.0702 .9314 .4009 .091 Uiso calc R 1 . . H H13F 1.1051 .8360 .5072 .091 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 .0835(14) .0633(13) .0603(12) .0207(11) -.0185(10) -.0021(10) N1 .100(2) .0637(18) .0753(18) .0127(16) -.0191(15) .0025(15) N2 .0523(13) .0602(14) .0472(12) .0020(11) -.0079(9) .0056(11) C1 .0486(14) .0600(18) .0372(12) .0031(13) .0012(10) .0035(13) C2 .0491(14) .0542(16) .0384(12) .0015(13) .0015(10) .0068(12) C3 .0577(16) .0655(18) .0417(13) .0068(14) .0001(12) .0023(13) C4 .0570(16) .0620(17) .0410(13) -.0002(14) .0029(12) -.0055(13) C5 .0538(15) .0637(18) .0374(12) .0016(13) .0034(12) .0001(12) C6 .0575(17) .0609(19) .0457(14) -.0014(15) -.0059(12) .0058(14) C7 .0517(14) .0537(16) .0332(12) -.0066(13) .0053(10) .0003(11) C8 .082(2) .067(2) .0463(15) .0068(17) -.0049(14) -.0102(14) C9 .085(2) .076(2) .0685(19) .0271(18) -.0049(17) .0016(18) C10 .0617(19) .094(3) .0497(16) .0131(18) -.0034(13) .0090(17) C11 .0592(17) .085(2) .0429(14) -.0154(16) -.0048(12) -.0057(15) C12 .0585(16) .0569(17) .0477(14) -.0055(14) .0040(12) -.0053(13) C13 .0569(17) .086(2) .0557(16) -.0011(16) -.0146(13) -.0020(15) O1' .0752(13) .1020(16) .0283(8) -.0310(11) .0014(8) -.0067(9) N1' .115(3) .183(4) .0527(16) -.072(2) -.0178(16) .000(2) N2' .0511(12) .0631(14) .0287(9) -.0101(11) .0017(8) -.0056(10) C1' .0490(14) .0551(16) .0294(11) -.0039(12) .0033(10) -.0067(11) C2' .0435(13) .0585(16) .0335(12) -.0036(12) .0013(10) -.0055(12) C3' .0564(16) .0710(19) .0436(14) -.0109(15) -.0010(12) .0047(14) C4' .0615(18) .0609(18) .0516(15) -.0017(16) .0055(13) .0070(13) C5' .0578(17) .0577(17) .0514(15) .0018(15) .0097(12) .0058(13) C6' .0627(18) .089(2) .0461(15) -.0277(16) -.0028(13) -.0014(15) C7' .0516(15) .0491(15) .0432(13) .0015(12) .0088(11) -.0003(12) C8' .0647(18) .0573(17) .0514(15) .0020(15) -.0036(13) .0037(13) C9' .0526(17) .086(2) .074(2) -.0091(17) -.0054(14) -.0035(19) C10' .070(2) .072(2) .081(2) -.0176(17) .0198(17) .0017(18) C11' .075(2) .069(2) .0672(18) -.0007(17) .0146(16) .0179(16) C12' .0596(17) .0593(17) .0515(15) .0030(14) .0046(12) .0060(13) C13' .0591(17) .073(2) .0506(14) -.0145(15) .0117(13) -.0041(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.213(3) yes N1 C6 . 1.138(4) yes N2 C1 . 1.332(3) yes N2 C13 . 1.466(3) yes C1 C2 . 1.513(3) yes C2 C3 . 1.346(4) yes C2 C6 . 1.423(4) yes C3 C4 . 1.414(4) yes C4 C5 . 1.199(3) yes C5 C7 . 1.424(4) yes C7 C8 . 1.378(4) no C7 C12 . 1.391(3) no C8 C9 . 1.381(4) no C9 C10 . 1.375(4) no C10 C11 . 1.351(4) no C11 C12 . 1.383(4) no O1' C1' . 1.228(3) yes N1' C6' . 1.131(3) yes N2' C1' . 1.329(3) yes N2' C13' . 1.450(3) yes C1' C2' . 1.495(3) yes C2' C3' . 1.335(3) yes C2' C6' . 1.420(3) yes C3' C4' . 1.411(4) yes C4' C5' . 1.191(4) yes C5' C7' . 1.432(4) yes C7' C12' . 1.385(4) no C7' C8' . 1.393(4) no C8' C9' . 1.365(4) no C9' C10' . 1.366(4) no C10' C11' . 1.371(4) no C11' C12' . 1.362(4) no N2 H2 . .8600 no C3 H3 . .9300 no C8 H8 . .9300 no C9 H9 . .9300 no C10 H10 . .9300 no C11 H11 . .9300 no C12 H12 . .9300 no C13 H13A . .9600 no C13 H13B . .9600 no C13 H13C . .9600 no N2' H2' . .8600 no C3' H3' . .9300 no C8' H8' . .9300 no C9' H9' . .9300 no C10' H10' . .9300 no C11' H11' . .9300 no C12' H12' . .9300 no C13' H13D . .9600 no C13' H13E . .9600 no C13' H13F . .9600 no